Acetic Acid → 1-Indanone

HRID 484246

반응식

HRID 484246 반응식
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH3:12])[C:8]2=[O:11])=[CH:4][CH:3]=1.C([CH2:15][C:16]([OH:18])=[O:17])#N.C(O)(=O)C.C1(C)C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C.O>[OH:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][C:7]([CH3:12])=[C:8]2[CH2:15][C:16]([OH:18])=[O:17].[C:8]1(=[O:11])[C:9]2[C:5](=[CH:4][CH:3]=[CH:2][CH:10]=2)[CH2:6][CH2:7]1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 1140TolueneHCID 9740Cyanoacetic acidHCID 2343386-Hydroxy-2-methyl-2,3-dihydro-1h-inden-1-one

생성물 2

HCID 67351-IndanoneHCID 199357125-Hydroxy-2-methyl indene-3-acetic acid

시약·촉매·용매 2

HCID 962Water용매HCID 21226138Dichloromethane ethylacetate용매

실험 절차

A mixture of the indanone (1.81 g, 11.17 mmole) of Example 1, Step D, cyanoacetic acid (1.05 g, 12.3 mmol) ammonium acetate (0.17 g), acetic acid (0.66 g) and toluene (5 mL) is heated at reflux with water removal (Dean-Stark) for 24 hours (TLC, CH2Cl2 -ethyl acetate 8:2). The toluene is evaporated and the residual yellow solid is redissolved in ethanol (6 mL) containing 2.2 N-KOH (1.4 mL). A solution of KOH (2.2 g, 85) in water (15 mL) is added and the solution is refluxed under nitrogen for 18 hours. The ethanol is evaporated, the residue is diluted with water and extracted with ether (2 times). The aqueous layer is acidified in the cold with 6N-HCl (to pH 3) and extracted with ethyl acetate. The extracts are washed with brine, dried (MgSO4) and evaporated to provide the crude title compound together with traces of unreacted indanone. It is used as such in the next step.

후처리

  1. temperatureis heated
  2. customThe toluene is evaporated
  3. dissolutionthe residual yellow solid is redissolved in ethanol (6 mL)
  4. additioncontaining 2.2 N-KOH (1.4 mL)
  5. additionA solution of KOH (2.2 g, 85) in water (15 mL) is added
  6. temperaturethe solution is refluxed under nitrogen for 18 hours
  7. customThe ethanol is evaporated
  8. additionthe residue is diluted with water
  9. extractionextracted with ether (2 times)
  10. extractionextracted with ethyl acetate
  11. washThe extracts are washed with brine
  12. dry with materialdried (MgSO4)
  13. customevaporated

출처 및 근거

ORD 기록
ord-fc106dec325241189ea2474522075811
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05229516

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